5-methyl-1-phenyl-1,2-dihydropyridin-2-one

• ChemBase ID: 70523
• Molecular Formular: C12H11NO
• Molecular Mass: 185.22184
• Monoisotopic Mass: 185.08406398
• SMILES: c1(=O)ccc(cn1c1ccccc1)C
• Canonical SMILES: Cc1ccc(=O)n(c1)c1ccccc1
• InChI: InChI=1S/C12H11NO/c1-10-7-8-12(14)13(9-10)11-5-3-2-4-6-11/h2-9H,1H3
• InChIKey: ISWRGOKTTBVCFA-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-methyl-1-phenyl-1,2-dihydropyridin-2-one
• IUPAC Traditional name: pirfenidone
• Synonyms: 5-Methyl-1-phenylpyridin-2(1H)-one; Pirfenidone; 5-Methyl-1-phenyl-2-(1H)-pyridone; Pirfenidone; 5-Methyl-1-phenyl-2(1H)pyridinone; 5-Methyl-1-phenyl-2(1H)pyridone; AMR 69; Deskar; Perfenidone; Pirespa; Pirfenidone; 5-Methyl-N-phenyl-2-1H-pyridone [Pirfenidone]

Database IDs

• CAS Number: 53179-13-8
• MDL Number: MFCD00866047
• PubChem SID: 24278625; 162036238
• PubChem CID: 40632
• ATC CODE: L04AX05
• CHEMBL: 1256391
• KEGG ID: D01583
• Wikipedia Title: Pirfenidone

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 2.1418576
• LogD (pH = 7.4): 2.1418576
• Log P: 2.1418576
• Molar Refractivity: 57.0016 cm^3
• Polarizability: 21.37245 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 10 mg/mL at 60 °C in water; 20 mg/mL in DMSO; Acetone; Chloroform; DMF; DMSO: >20 mg/mL; Ethanol; Ethyl Acetate; H2O: >10 mg/mL at 60 °C (warming for 30 minutes); Methanol
• Apperance: Off-White Solid
• Melting Point: 108-110°C

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• RTECS: UV1148200
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R22
• Safety Statements: S36
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: Smad; TGF-beta

Product Information

• Purity: ≥97% (HPLC); 95+%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C12H11NO

DETAILS

Sigma Aldrich - P2116

Biochem/physiol Actions
Pirfenidone inhibits collagen production and fibroblast proliferation. It has shown antifibrotic and anti-inflammatory properties in variety of animal models of pulmonary fibrosis, and in clinical trials.

Toronto Research Chemicals - M325896

Pirfenidone has demonstrated activity in multiple fibrotic conditions, including those of the lung, kidney and liver.

REFERENCES

• Mitch, W., et al.: Lancet, 2, 1326 (1976)
• Iyer, S., et al.: J. Pharmacol. Exp. Ther., 291, 367 (1976)
• Al-Bayati, M., et al.: Biochem. Pharmacol., 64, 517 (1976)
• Gahl, W., et al.: Mol. Genet. Metab., 76, 234 (1976)